Whether leading a team of nine or nine thousand, leadership requires self-awareness, empathy towards those you lead, being mindful how messages resonate, and sharpening your leadership values into relatively quick, practical insights. Special guest Major General USAF (Retired) Brett Williams shares his views on all of these topics and more with co-hosts Brian Comerford and Nick Lozano, as they discuss the development of his leadership acumen across domains as complex as the U.S. Air Force's largest combat wing in Okinawa, United States Cyber Command, or his tech startup, IronNet Cybersecurity.

Brett T. Williams
Major General, USAF (Retired)
Chief Operating Officer
IronNet Cybersecurity, Inc

LinkedIn: https://www.linkedin.com/in/et183394/

Brett Williams is a co-founder and the Chief Operating Officer at IronNet Cybersecurity.  IronNet delivers the power of collective cybersecurity to defend companies, sectors and nations.  Their advanced cyber detection solution leverages behavioral analytics, artificial intelligence and machine learning to protect against the most advanced threats.  As COO, Brett supports strategic planning, leads business performance management efforts provides thought leadership to support marketing and sales.

During his time as an Air Force General Officer, Brett served in four senior executive leadership positions.  As the Director of Operations (J3) at U.S. Cyber Command, he led a team of 400 people responsible for the global operations and defense of all DOD networks as well as the planning and execution of authorized offensive operations.  Prior to this position, he served as Director of Operations (A3O), U.S. Air Force, where he led the largest Air Staff directorate consisting of more than 1300 Airmen and civilians stationed world-wide.  In this role, he developed and justified the operations component of the annual $120B Air Force budget. General Williams also served as the Director of Communications (J6) for U.S. Pacific Command. His 150-person directorate executed an annual budget of $57M and was responsible for the design, implementation and operation of all command and control networks supporting DOD’s largest geographic warfighting command.  Finally, as the Inspector General for Air Combat Command, he led the inspection, audit and compliance process for all U.S based combat flying organizations.

Operationally, General Williams led a variety of large, complex organizations ranging in size from 300 to over 9000 personnel.  In his most significant leadership position as 18th Wing Commander in Okinawa, Japan, he led the largest combat wing in the Air Force. General Williams was responsible for relationships with Japanese political and business leaders in a highly volatile community environment. He executed an annual budget in excess of $100M to support a community of over 25,000 U.S. service members, their families and Japanese employees.  In this significant leadership role, he delivered success across a wide variety of mission areas to include aircraft operations, aircraft maintenance, logistics, civil engineering, security and policing, community support, human resources, financial management and medical services.  Brett is an F-15C fighter pilot with over 28 years of flying experience, including more than 100 combat missions.

Brett is a highly regarded keynote speaker, leadership coach, and cybersecurity expert.  He has appeared several times on national television, testified before the Senate Armed Services Committee and is a sought-after subject matter expert.  Brett has served as a faculty member with the National Association of Corporate Directors Board Advisory Services as well as a guest professor at Duke University.  He has served on the Defense Science Board and on a variety of corporate advisory boards.  Brett holds a BS in Computer Science from Duke University and three graduate degrees in management and national security studies.

0:08 Opening
2:36 Brett Williams, Maj Gen USAF (Ret) Intro
12:41 Technology is the Backbone of Business
15:56 The Five Things New Leaders Should Do
23:48 Developing Talent
31:10 Learning Styles
33:49 Leading Multi-Generational Teams
41:01 The Importance of Cyber Security to Leaders
48:31 Recommended Books
59:01 Where You Can Find Brett Williams, Major General, USAF (Retired) and Closing

Hosted By:

Brian Comerford
LinkedIn: https://www.linkedin.com/in/briancomerford/

Nick Lozano
LinkedIn: https://www.linkedin.com/in/nick-lozano-97356621/
Twitter: https://twitter.com/NickLLozano

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Show Transcript:

Nick Lozano  0:08
So Brian, we had a very interesting guest today probably, you know, one of the guests who's had the most diverse background out of any of our guest and one who kind of cut their teeth and leadership in the military.

Brian Comerford  0:24
And I've got to say, you know, it's humbling to hear about some of the scope of the leadership responsibilities that Brett Williams, Major General, retired US Air Force, who has been speaking with us today, just the scope of his leadership responsibilities. But the interesting thing is, as we continued to talk, and you distill it down, it's the same themes of everything that you and I have talked about with so many of our other guests and that you want I have experienced and, and share just as you and I have talked together on this podcast, that there are just a specific group of themes that seem to be universal. With technology and leadership. Part of that is about making sure that you have a seat at the table, regardless of what kind of industry or and, and so to hear someone with the breadth of experience that he had in the United States Air Force, speaking to that same kind of theme. It was, it was somehow validating it at the same time that it was really enlightening.

Nick Lozano  1:38
You know, as I was doing my homework on him before we hopped on the show, and I went to his website, and he had this great quote, it says technology changes every day, but technology will never be replaced by good leadership. That's kind of where we are even with our theme of this podcast. So I guess with that, Brian, it's a good spot, you know, to just, you know, hop off here and let our you know Listen, the show.

Brian Comerford  2:01
Sounds great.

Thanks for joining us for another edition of lead.exe. I'm Brian Comerford in Denver, Colorado.

Nick Lozano  2:13
And I'm Nick Lozano in Washington DC.

Brian Comerford  2:16
And we're joined today with our special guest, Brett Williams, Major General USAF retired and current CEO of IronNet cyber security. We're going to chat with him about a broad swath of topics today. I'm confident. Thank you very much, Brett, for joining us and take time out of your busy schedule.

Brett Williams, Maj Gen USAF (Ret)  2:36
That's great, Nick and, Brian. I appreciate y'all giving me the opportunity to chat with you today. I look forward to the conversation.

Nick Lozano  2:43
Appreciate it. Thank you for coming.

Brian Comerford  2:45
Yeah, absolutely. Well, looking at the schedule you keep it looks like you know, every hour is precious. So we're particularly appreciative of you sacrificing a sliver of it with us. So you know, part of what I learned in reading a bit of your back background is you started off as a fighter pilot. So probably cyber security was far from anything that you were necessarily thinking about in your early days in the Air Force. Can you can you tell us a little bit about even how you started thinking about a career in the Air Force and where that led to becoming a pilot? Yeah, absolutely.

Brett Williams, Maj Gen USAF (Ret)  3:21
Um, you know, this is a question I get a lot, especially from younger folks, and I feel bad that I can't answer it very well. I've, in fact, I've gone back to my high school yearbook and I've looked through there to try to find the picture of the guidance counselor who told me Are you interested in flying? Well, maybe not apply for an ROTC scholarship and apply to be a pilot and have you thought about where you're going to school you ever heard of Duke University, you know, and I know so I applied for the scholarship. I applied to be a pilot I applied to the Duke I got accepted all those. That's good enough. And, you know, off I went, and you know, this was obviously well before the days of The intense college application process that we have today but so off, I went to Duke University. My wife and I both graduated from there. She commissioned into the air force the same day I did. She served for 20 years there for 33 years, and now we've been married for 38 years. I've got, I've got two kids. I've got a daughter that works in banking. And I've got a son who also didn't want a real job. He's a fighter pilot. He's, he's an F 16 pilot, down at the shot Air Force Base and in South Carolina, and he's married and his wife works in construction management. So so that's a little my personal background. But yeah, so I started off as an F 15 pilot and kind of the way it works. If you make the normal progression and end up where I did is, you can think of it as your first 10 years or so you're an individual contributor, more or less, right here. 15 pilot, you're being the best pilot you can you're upgrading to flight lead instructor pilot. And it was really I always make this point that and I just learned this word reading bill George's book about true north, this word called generativity, which is there's three three stages of leadership. There's learning to be a leader, there's leading and then there's generativity, when you feel this, this desire to train the people that are going to replace you, etc. And when I read that I figured out that didn't have anything to do with being old. It had to do. It had to do with when you became proficient at a certain level, and you started to teach other people to do the same thing at a higher level, that that's when you really start getting the satisfaction of growing the leaders that will replace you so so when I became a proficient instructor, I went to something called the Air Force Fighter Weapons School, which is what a lot of people equated to Top Gun in the Navy the fighter weapons school in the Air Force is much more difficult and longer but anyway I'll leave that alone. You know as a as a captain in the Air Force when I became a pretty proficient instructor, I of course still greatly enjoyed doing well myself and flying the airplane well, but I found I took all sorts of pleasure in you know, teaching that new wingman to fly, you know, and so now as, as I continue to my career, you you start to broaden, you become a commander, my first command was a squadron at Langley Air Force Base, about 350 people but you know, 50 of those are the motorcycle gang, the pilots, right, the other 300 were the you know, all the people that maintain the airplane. So that was my first real taste of cross generational leadership because they're all 18 to 25 years old, is my first taste of real responsibility outside of just executing the fighter mission, which is tough in itself, you know, but now you are responsible for leading all of these people for making decisions on you know, the terms are the same are different in the private sector, but you're doing talent management, talent acquisition, you're doing feedback, you're doing performance development, you're providing vision, motivation, budget, you know, all of those things. And, and you're, you're, you know, you're running an organization that is much different when people think of, oh, you're a fighter pilot. Right, though, you know, as I progressed through these things, my my last operational job, I was command in the Air Force's largest combat wing, that's it Kadena Air Base in Okinawa, Japan. And I've been found out over time that again, even as a general officer, the average person in the public doesn't understand what that that means. So just to give you a taste of what that job was, like, about 9,000 people in my command, of course I had there are five different types. Airplanes there, one of which was the F 15, which I continue to fly and I'm proud to say was an instructor still my advanced age and then we still had the operators, the people that aircrew the flew the airplanes, the maintenance people, but now I had, for instance, I had 1500 civil engineers. I had a 500 person hospital, I had a 2000 persons support group that did security training, ran our legal system, handled the 2000 Japanese employees that worked on the base every day. And then on top of that, you know, it's kind of the mayor of this community at 25,000 military people and families and stuff that lived over there. And if you don't know, Okinawa is one of our most difficult overseas locations because the politics are they're so tough over there. The Okinawa people are awesome, but they bear what they call the burden of hosting most of the American forces over there. So, so, you know, you look at that job and you look at you know, what, certainly You know, there's a lot of Fortune 1000 businesses that you could run that maybe don't have that span. You know, and that sort of thing. So, so I share that, because I found it necessary to kind of anchor people. And, you know, and I wasn't unusual, you know, if you make that, that that rank those the kind of responsibility you're expected to be able to, you're supposed to be expected to lead large and diverse and complex organizations. So. So it came time for me to leave there. And I got a call from my boss, the four star general down in Hawaii, I was a one star and he says, you know, it's time to leave and you're going to be going and working at this place called Pacific Command, which was headquartered in Hawaii, but they were the command that was responsible for all operations in the Pacific, not just Air Force, but Army, Navy, Air Force, Marines, and you're going to be what's called the J Six and if you don't understand how military staffs are organized, the one is day ones intelligence or I'm sorry, day one is Personnel twos intelligence threes operations where I thought I should be working force logistics, fives plans, they'll be a test later, six. Six is where all the cool people work the IT people the command and control systems, the cyber. And so what that was was the I would argue the first recognition by one of our four star senior commanders that we had to stop looking at it and cyber and all of that as a support function, right? You can't have forces spread over 52% of the Earth's surface, as we like to say, and if you can't command and control them, right, if you can't issue orders, make sure they get to the right people that they don't get to the wrong people that when they get there, they're modified that they get there on time, etc, etc. If you can't do that, then you are going to execute your mission. Okay. And so his view was we've got to put somebody in there from an operational background. So we can operationalize this function. And then what I found out very quickly after getting the job is that the people that worked in there, they were We're more than smart enough to do this. The problem was, nobody ever invited him in the room unless the video teleconference didn't work, right. So on one hand, you are potentially delegating strategically important decisions to very junior people who have no idea what the mission priorities are not because they're not smart enough, because they're never invited in the room. So as I reflect on my five years now in the private sector, working all sorts of, you know, in my company, but through a variety of different things, I have worked with all sorts of other companies. The dynamic is exactly the same people are realizing that you don't run a business, I don't care what size it is without being able to operate in cyberspace, right? Yet, they still struggle. Why can't the CIO talk in business terms? How come they can't talk to the board Make sense? You know, blah, blah, blah, blah, blah? Well, if you ever brought them in the room when you had a significant business discussion, etc, you know, so that's changing, especially some of the bigger companies But a lot of other companies, you know it, it's not and so, so I spent the last five years my career doing mostly cyber and it I finished at United States Cyber Command. So I was responsible for operations and defense and planning offensive operations for the Department of Defense. And then when I retired a co founded our net cyber security with with my former boss, he was the Director of the National Security Agency. And so we've, we're about five years into our startup journey, and we're learning what everybody learns it costs more and it takes longer than you would like, but we're, we're doing well, we're growing and you know, and that's where I am today.

Brian Comerford  12:41
It's fascinating Brett, thank you so much for sharing that background. And and I was missing, not saying thank you for your service and thank you to your your wife and son as well. Well, thank you. That is just astonishing in scope, but it's also reassuring to a degree to know that That, even at that scale, the the challenges are really no different than many of the things that Nick and I have talked about for, you know, 4,050 person organizations. And certainly the constraint that you identified around, who do you bring in to have a seat at the table, whether or not you believe you're a technology company, if technology is truly the backbone, and part of your delivery mechanism that your entire business is dependent upon, you should probably be strategizing in a different way when it comes to inviting technologists to be part of your executive council.

Brett Williams, Maj Gen USAF (Ret)  13:37
Exactly. You know, what I found in the military, and then as I've worked with, I've been in a about 15 or 16 boardrooms, working with the National Association of Corporate Directors. So go in and do anywhere from two to four hours with the board on managing cyber risk and all that. And I make the same point to these board members that I made to the three and four star generals is that You need to have an adult conversation with your technology leaders just like you do with your CFO, your general counsel and your CEO, right. I talked about you can't have a Barney style conversation and depend on the depend on your generation that's either Barney the Dinosaur or Barney Fife. But, but but you know what I mean, Brian, if you're my CFO, and I'm on the audit committee, or I'm the CEO, I know exactly what to ask you. And I know if the answer makes sense, right? And if I'm talking to the CEO, the same thing, but then if I go to Nick, and he's my CIO, then I go, Hey, Nick, is everything good? Right. And it seems saying that's a completely different dynamic. So what I what I tell them is that you know, you have got to take time to learn some of the basic concepts, the terms, that sort of thing. So you can make the same strategic risk decisions involving not just cyber but Technology writ large. And now I'm, you know, as we talked about a little bit earlier, I'm really looking for the kind of how to share some of this in a broader perspective, just beyond cyber security and broader leadership context. I've kind of been playing around with this thought that and it really comes off what you just said, Brian is, every CEO today is a tech CEO, or at least they should be right. Or they should be. And that doesn't mean you're a tech leader. That's a different context. But as a CEO, you have to be technically aware, you have to be technically conversant. You have to understand how technology, what benefits it brings to my company, and what risks I'm incurring by using this technology because all of it comes with both sides. Right risk. And that's, I think that's the name of the game there.

Nick Lozano  15:56
I love that I and I think you bring up a good point, and I think Dominio's Pizza has actually been a big player in that, right? They always say they're a technology company first, who just happens to sell pizza. Right. And I mean, I think that's a huge point. And, you know, you kind of brought up your experience and and when I was poking around and kind of doing my research, you know, you had this article that said the five things that you need to tell your your new team, and I thought that was a great, great article, and it was just good for anybody in general, when they're new on a team. You know, you said, Why am I here? What are my goals? How do I like to communicate? What am I going to change it when and what is my leadership philosophy? How did you come to those, those five things?

Brett Williams, Maj Gen USAF (Ret)  16:43
Well, one of the things that, you know, and we all learn by the leaders that we follow, but I had a when I was that squadron commander and kinda in the Air Force Squadron is the first then group and then wing. And so when I was a squadron commander, the wing Commander was the big boss and I remember his name was Steve Goldfine, Goldy Goldfine, you know, we all have callsigns. Nobody knows our real first name. But anyway, but so he brought us all in all of his squadron commanders, and he took 45 minutes and just went down this list of, you know, basically, here's how I do business, you know, and I did what I did throughout my career, which is I'm taking notes, right, I'm right now, here's things I see from leaders that really work and I want to emulate but just as importantly, everybody can serve as an example If only is a bad example. So you write down things that you will never repeat and do. So, so I have my list of things that whenever, you know, whether it was a command or you know, because we'd go to staff jobs and that sort of thing, things that I would convey and then back to this mentoring thing. In the same way I was an instructor pilot for F 15 pilots I became an instructor pilots for new commanders. So we had a course for you know, you're going Become the Wing Commander in Okinawa, you come in and we spend two weeks you know, talking to you about how to be a Wing Commander. So one things always passed on to them was, Hey, what are you going to say day one people want to hear from you. And so that specific article though Nick came from, I did a talk in New York City couple of weeks ago with a company called tech 2025. And it was very it was a great opportunity for me to talk leadership to a completely different audience you know, a lot of civilians all civilians obviously but you know, quite a few millennials some Gen Z years and you know, without breaking my arm patting myself on the back, but I spent an hour afterwards with people lined up to talk to me and, and one guy sent me an email and he said, Hey, his name was Carlos. He's in the post on LinkedIn. But he said, I'm taking over the organization here, what, you know, what should I do, and I pulled out my My list of things that I carried around I thought, you know, I've never actually written this down. So here you go, this is what I would. Here's what I would, here's what I would do. And that's the stuff I like to write about and talk about, like, you know, I love books like you know, this one I just recently read mentioned build George's book on truenorth a read another one hacking, life hacking, I think not too long ago. But you know, a lot of the leadership stuff i see i think is, I call it the philosophical stuff, which is really important. It's you got to know what you got to know yourself. You got to know what's important to you, you got to understand what values you won't compromise you got to understand what's my leadership styles as authoritative as a collaborative is it whatever, I gotta be mindful, I gotta be all of that. But the the, there's no but all that's important, okay. But what I find that I like to convey and seems to resonate the best is these relatively quick practical things, right. I'm going into a new organization, what should I do you know, Okay, here's five things I would make sure I convey people are going to ask this, you know, hey, I've got to do my first feedback session with someone who hasn't done too. Well, you know, how should I approach that? You know, those kind of things are the things that I like to write and talk about. So when I had that opportunity, I said, Well, let me write this down.

Nick Lozano  20:19
I really like that, because I'm a huge fan of, you know, just simple, easy things to remember. But, you know, like, I'll see people post something else will be like the 35 things a new leader should do. Remember 35 things? Right, right. Right, boil it down to the most, you know, the greatest five things I should do. I mean, that's, that's just a great list. I, I really think you should do, like put that in some type of like, print form. Yeah. And just kind of hand it out when you speak it. I mean, it's, it's a great resource, in my opinion.

Brett Williams, Maj Gen USAF (Ret)  20:48
Well, thank you very much. So that's awesome feedback. And, you know, started writing more and more of this on LinkedIn, just you know, I keep thinking as a book, the right thing to do, but it just seems so easy to run. But you know, there's so many books, they're just so much noise out there in general about leadership is, you know, how do you how do you get through with your message. And I think you just you just keep putting it out there till you see where it responds. And so just like this getting linked up with the opportunity to speak with you guys, because, you know, like some of the stuff. What I want the first things I saw on yours was you have that discussion on leadership versus managers, you know, and now, I remember in our companies, obviously, a tech company, we're building a software product, I hadn't been there very long, and I can still see it. You know, there's certain things that are in your memory. And you can see, I can see this conversation with these three software developers, and they're talking about how they don't want to be people managers. I said, Well, first of all, I said, You lead people and you manage resources. And I'm telling you, these guys are these guys are all 23 and they're looking at me dumbfounded. They have never heard this. They go, What do you mean, right? And I said, well, leadership is about relating to people. It's about understanding what makes them Move what gets them excited? Because you got to understand that if you're going to get them aligned behind the vision of the company, if you're going to be successful, all that resources you manage, which are time people and money, right, nobody has enough time. Nobody has enough peoples and nobody has enough money. Right? So the manager side of a leader, and I believe leaders have to be both. I don't know how much you want to go down this trail here, but irritates the crap out of me that when I see these discussions about all we have way too many managers, you know, you look at the org chart and there and I go, Well, I don't see how you, you know, you've got a team of eight or nine people that's doing whatever it is, and your company, that somebody is going to be the most experienced, right? They're going to come into the workflow, they're gonna do all that kind of thing. So so they're going to manage the team, but the same time, they've got to provide leadership because it's that next level manager that communicates the vision from the top down, that does the feed. Back in the performance assessment that makes sure that I know that, you know, Nick's ultimate goal is actually to move horizontally over into marketing at some point where Brian's goal is to move up and take my job. And Brett's goal is actually to leave the company in two years, because he wants to start his own thing. So it's that leader that understands what makes each person on that team tick so that as long as you have them there, you're getting the most out of them. But the way you get the most out of them is you position them to be wherever they want to be. So, you know, that's the leadership side, in my view, the manager side is, hey, we got too many, you know, everything can't be number one priority or you know, I need slack premium or you know, whatever it is. So, those kind of things. So, I love you guys. The context you put around. That is one of my favorites.

Brian Comerford  23:48
That's great. And thank you for the feedback. You know, this is I mean, such a strong theme for us and, you know, all the discussions that we have, whether we're talking with guy like yourself, whether we're working in another Leadership Forum, it seems to be one of those concepts that is, you know, once the light bulb goes on, people get it. But it's almost like developing people from that management mentality into that leadership, you know, thought domain. It's, it's really like there's some kind of transformation that has to take place there. For us, you know, really trying to discuss it, call it out through exercises. I mean, these are things that, you know, we've been passionate about ourselves and creating a curriculum where we're taking people who are Junior, right, who may never have even thought of themselves as "well, my next ambition is to go become a leader or a manager somewhere," and actually giving them practical tools through exercise, to be able to undergo that type of transformation. What have you found that is effective in trying to help develop talent in that way with folks that you've worked with.

Brett Williams, Maj Gen USAF (Ret)  25:08
I think step one is. And I'm just, I'm doing this at flight. I'm building the airplane as I fly. But you really prompted an interesting question in my mind. And it's not like I haven't thought about this before. But I was about to tell you, there's two components this but I just realized there's three. So I think the first thing you have to do is you've got to look at people and I think they fall into two, one of three categories, right? That they have potential to be a leader, and they want to be a leader, okay? They have potential to be a leader, but they don't want to be a leader, okay? And they don't have the potential to be a leader. So it doesn't really matter whether they want to or not, you've got to give them the feedback that says, you know, hey, This is going to be a really long road for you, you know, etc. and feedback is another area I'm passionate about. So I'll leave that that last category alone. But you know, the challenge there is the person that really wants to, like I've got a story I've told all the time about a young fighter pilot, he wanted to go to fighter weapons school, he won't be the greatest depth 15 pilots ever was ever secretary. But that just I knew it wasn't going to happen, you know, for him, but he had all these other skills. Right. And fast forward. 20 years later, he retired as a one star general, I was at his retirement. And he brought up that conversation that we had 25 years earlier and said I wouldn't have been as successful as I was, if I hadn't gotten that feedback because it told me These are my strengths. These garnered focus. Okay. So then that takes you to the other two, you know, the people that have the capability to be leaders and want to be leaders. Right, then, you know, the the challenge, then I think is, is understanding or helping them understand this isn't going to happen overnight. You know, that there's a lot of work you've got to do on your side. A lot of it is that reflection, what's important to you all that sort of thing. And then we have to come up with a plan together on how we're going to get you the experiences you need, you know, so that you start developing because the things I've read recently, I don't know if this numbers, right, I took, you know, something like $200 billion was spent globally last year on leadership training, and maybe $10 million of it can be proven to be effective. So you know, how effective I will send you off for three days, you know, we'll have a two day seminar, you'll walk out with a bunch of those little spiral boundaries, you know, those can be useful, but that takes you got to be deliberate about it. You got to get the value out of you know, those sorts of things. So for the people that can be leaders and want to be leaders, then we got to figure out the best way and each one is going to learn a little bit differently, right. I've recently run across a framework that says, you know, that that kind of leader development 70% of it ought to be on the job training right. Maybe you're an individual contributor. Now, I'm going to put you in charge of this project, right it last two months, you know, it's in your career failed, but these other two people are going to be working with you, but you've got the lead. So once a week, you're going to brief us, let us know how it's going, you know, that kind of thing. So you find ways, and that's mostly the way they learn to do it. But 20% of that learning is coaching, right? So you've got somebody that's really good at mentoring and coaching, because mentoring and coaching isn't the same as feedback, right? So if you work for me, Nick, and I'm doing a good job of feedback, then we're having routine conversations, you know, every couple of weeks, we've got some specific goals we've set you know, I've written some of this on LinkedIn too. But then, you know, there's some formal feedback that happens, etc. If I'm going to really be coaching or mentoring you on your, your leadership, it needs to be deliberate. It needs to be specific, because if we're working together every single day, then you're trying to do things better. You're trying to do things different. You're trying to reach out I'm probably not going to see that because I know what next like, I gotta you know, so if I'm going to be your coach and mentor, I almost have to be somebody who's not in your, your, your managerial change, somebody that's really observing is qualified to observe, right? And now I'm sitting kind of as that third party, if you will, looking kind of peripherally at this and say, you know, here's what I see, here's what I hear, you know, that kind of thing. And so 20% of it's got to be that deliberate coaching and mentoring but that's not an easy job, you got to have the right people doing that. And then 10% is, you know, this, the more formal training and that has to be done in a way. I don't know if you're familiar with the Center for Leadership Studies, they had the situational leadership model. So good friend of mine, Sam shrivers, the COO there and actually had them into our company and full disclosure about a year ago very well received. That was an interesting one because I people come up to me a lot of tech people two or three months later and go I had no idea that that I needed something like that. But I just so appreciate getting that leadership training right then to that that other person, the one that thought they never wanted to be a leader, I can think of all sorts of examples in my military career where there were people that could you get to a certain level. There's things you have to volunteer for, you know, most things, you're voluntold like, you know, there's there but there's certain positions that you have to volunteer for. And I had a senior enlisted woman who done just a great job and she would been perfect to take this other role. And I'm sorry, I just don't want to do that. Blah, blah, blah. So I kind of twisted her arm, you know, and eventually did it and she took that and there are different levels of that she took that up like three more positions ended up retiring as a Chief Master Sergeant was one of the best there is that what we call this command, Master command Chief Master Sergeant position. So so I think that's a long way of getting at. If you're going to train people, right? First of all, you got to figure out what kind of person they are and Then it's got to be, it's got to be deliberate. It's got to be planned. And frankly, not just anybody can do it, you got to have people that understand how to coach and mentor, I think.

Brian Comerford  31:10
I think that's a great answer. And I think it also, you know, resonates with something that Nick and I have talked about, you know, quite a bit, which is the the training component, having some kind of exercise to help take what's theoretical and immediately put it into action so that you're developing some muscle memory around it. Because there's so many different learning styles, right? I mean, people, some people, they need to listen, they need to take notes, some people they need to see something visual, some people are kinetic, and they actually have to interact with something before it really makes sense. So having a learning model that encapsulate as many of those different types of learning styles as possible as I think is also a valuable facet to consider.

Brett Williams, Maj Gen USAF (Ret)  31:51
Yeah, no to that that point, Brian, you know, everybody, not everybody but you know, people who have been successful at at, you know, leading or managing whatever It is and then they go, you know, so I'll just be a coach or one better, you know, you gotta have some kind of gotta have some kind of model, you've got to have some disciplined way to approach this because, you know, otherwise I can't just, you know, hop on the phone with you and start going, Hey, how's it going? You know, so there's got to be, you know, there's got to be some disciplined way to go after this and then and then I think that while I think a lot of the cross generational stereotypes we bring up aren't necessarily valid because I read stuff about what boomers are and I go I don't look anything like that. So what makes me believe more titles look anything like this. Right? So so I think a lot of that is is has to be taken with a grain of salt but I do think to your point, you reminds me of the golf analogy I you know, I play a lot of golf is that, you know, when you teach somebody play golf, some people you got to put your hands on them, you know, some people they watch somebody else do it and then some people here I want you to do this right. People are role playing Helps really well, some people watching scenario on a video works really well, some people reading about it, having to write it out, you know, all sorts of different things. So I think to your point, I think the point you're making is if you're going to be effective at this, you got to have several different ways to teach the same thing. But they have to have, I think a way, like when I do my keynotes, you know, on cyber, I know I'm getting successful when you see him reach for that little pad of paper that's underneath the fence in the middle of the table, you know, bring it back and they start writing stuff down. Because my goal is you walk out the door with three things, when you go back to your company, you start doing so same thing with a leadership training thing. I want them to walk out the door with three things I can do different today. And I can see if it works. I've got a way to measure whether it works, you know, that sort of thing.

Nick Lozano  33:49
And I just want to bring up you brought multigenerational you know leading teams and it kind of seems like you know, for a while the millennials have been bashed on and now now even The baby boomer generation is being bashed on by the younger generations with the Okay, Boomer thing. I don't know if you've seen that. Oh, yeah. But um, you know, and Generation Z. And just in my experience, you know, most people always kind of want the same things, don't it? Doesn't everyone want to know what their mission is? Doesn't everybody want to be doing something better than themselves contributing to something great. But I mean, in your experience, you know, because you've led hugely large teams. What are some of kind of your takeaways from leading the multi generational team? I mean, I know just between generations, things are always going to be different, right? Just because everyone's experience and time is different. But I'm wondering, what are some of the things that you have learned that you can, you know, give to our audience?

Brett Williams, Maj Gen USAF (Ret)  34:45
I think there's several things in no particular order. I think one of the most important things that you've got to understand is, is as a leader communication and you know, one of my favorite sayings about that is it Doesn't matter what I say it matters what you heard. And so one of the first things I've got to do, even if I'm leading a team of everybody the same age, but especially multi generational like that, is, you know, the message that I'm putting out at the top of the organization, how do I know what message is received at three levels down, and the only way to know that is to get out and walk around and talk to people, right? Because I can't go out and personally, you know, 9000 people, I can't personally go out touch each one of them, you know, and, you know, there's, there's leadership theories or management theories that, you know, that, you know, once you get beyond eight to 10, direct reports, right, you can't have a direct influence on you know, many more people than that. So you've got to have a way that that that message cascades down. And so, having a way to check that your message is getting out in the way you want it to get out. And that doesn't mean it has to be verbatim, right because, you know, if we just took the, the, you know, the, the boomer running the organization and then he's got the You know, the Gen X or s, you know, VP and then he's got, you know, the senior millennials and the junior millennials and the Generation Z years down here, you know, that, that, you know, somebody a couple of levels below me is going to be possibly better at communicating to that brand new employee and words that makes sense to them. But I have to make sure that the vision, the you know, the basic things that we want to have happen that they get, they get translated in the right way. But at the same time, I found that, you know, I mentor Duke students out here, I work with a lot of ROTC cadets, I, I, I think you should just talk to people and you you spend a little bit of time understanding their world that you know, you can communicate. One thing that struck me over the last couple of years between both working in my company and with some of these other groups I work with is, is these 25 year olds are dying for leaving Leadership stuff. I really see it in formal conversations, informal conversation. So I think there's a huge opportunity but, but to me, the biggest thing is communication. And I think it's learning to use other communications, that means that maybe you haven't been comfortable with in the past, you know, the whole quote unquote, social media, you know, that goes all the way from, you know, Facebook, and that kind of thing to how does your company use slack or what's involved in Microsoft one team, you know, those are social media things. We use an HR platform called, called quantum and I primarily drive it so people are individual goals in there, but that becomes because, you know, it's got likes, and it's got posts, and it's got shout outs, it's got all that so, so to me, that's where the boomer you know, or the Gen Xers got to figure out, you know, how can I leverage those platforms to make sure I'm both not both to make sure I'm communicating remember that communicating is Some of its talking but most of its right listening and making sure you get that message back. So to me, the biggest thing is, it is about communication. But the second thing is, is that kind of to your point earlier, Nick is, again, the example I use, we got a 25 year old software developer, he's a rockstar, right? He's one of our top two or three folks. And there was a period of time when I was overseeing our engineering area, and not that I have any expertise in that, but we needed somebody to go in there, you know, as we were looking for the right, lead for that area. And you know, I started read about agile and reading about Scrum and reading about some of these ways to, you know, set objectives and get more specific and requirements and all this kind of stuff. And, you know, and there were some pushback, I know, we don't want to do that too much process to make you agile, right? And he came up to me, he goes dope. He says, Don't let them when we're on the right track. I mean, He said without planning without process or out requirements, we call that chaos. Right? And so this is this, you know, this young guy who absolutely was looking for what's the direction? What are the priorities? How do I how do I contribute? So I think you're exactly right. Everybody wants to know and then I call it connecting the dots. How does what I do every day contribute to the, to the mission of this, this organization and not to kill you guys with stories but during Desert Storm to Operation Iraqi Freedom, so I'm over at a base in Saudi Arabia is literally in the middle of the desert. I had the ops group at the time one below the wing so about 2000 different people flying all sorts of different airplanes and stuff. And we all operate in this place called ops town right? That's where all the air crew work. But whenever the calm guys came in, even to fix a phone, they were fired up. They are professional because somehow their boss had conveyed to them how important their job was right? Because it's not hard to convince the pilot, how important his or her job, it's not hard to convince the person load the bombs on the airplane, you know, they can connect that to the airplane taken off and go on this mission. But the kind of fixes the phone, how do you convince him and then draw that back to there were literally people that deployed for a year to work in the gym handing out basketballs. So look at the leadership it takes to make that person understand their connection, right, they got a lot more dots to connect. So so I think that's another thing people want is helped me connect the dots from what I do to this company generating revenue. And, and as a leader, you should be able to do that you should be able to help them figure that out. And when they come to work motivated, that way, you're going to get a lot more out of them than just, you know, am I making more than my buddy over it, you know, ABC software

Brian Comerford  41:01
That's awesome. And, you know, I want to make sure that we give a little bit of time to your current area of work in cyber security. And that's, that's a topic that I think, you know, anyone in any company, whether it's a forthright technology company or not, you know, security is top of mind for a lot of folks. There are a lot of leaders who really are scratching their heads and don't even know where to start in some of your engagements with your current company, and kind of blending that with some of these leadership techniques that we've been discussing. What are some of those things that are the most critical areas that you feel like you know, someone who's in a leadership role, but they may not understand the importance of security? What are those key takeaways that they need to understand for their own organization?

Brett Williams, Maj Gen USAF (Ret)  41:50
Yeah, that's a that's a great question. And I'll start that with a conversation I had earlier today. I was talking to guys write an article for a magazine. I know you guys read frequently. It's the general counsel journal. You know, he's writing an article for the general counsel journal, and it's about, you know, where does managing cyber risk belong in the company? You know, super important question, what's the role of GCS and doing this and all that stuff. So, so super important. And I give you the example, just to show this has been worked on, you know, there's a lot of people thinking really hard about this, but the, I think there's two sides of this on the business side, you have to take the discussion away from cyber security to to really risk management. So like, when I would go into these boardrooms, I always started with a discussion of enterprise risk management, you know, and just kind of, I would review their enterprise risk management, you know, how have they done it? What did they, you know, go in there, what's that thing called their, you know, their SEC filings, and we list whatever the, you know, risks are and all that kind of stuff. And I would tell them nine times out of 10 I said, I don't see cyber security risk is any of your strategic risks. I said, Did you hear about Yahoo, they dropped $350 million dollars in value in two months from the time this leak was but, you know, millions and millions of dollars 60% of small and mid sized businesses are out of business after six months following a breach, right? That How can this not be a strategic risk for you? Right? And so you start down that discussion. And so it becomes, it's not the most important, but it should be one of the strategic risks you are concerned with, right? Because your attack surface is so big, right and understand it and you have to understand the cost, right? Because most people think, well, the cost is to, you know, recover this data or pay for identity insurance or whatever. But that's just the tip of the iceberg, right that the next level of cost is the liability costs. You know, you To have a slide I showed it was four years after the target hack, and they're still settling lawsuits about who's going to pay to replace the credit cards, right? So the liability side of this is huge, right? And then real intangible cost here is things like reputation cost, the operational costs, in other words, you can recover from this, this breach whatever it was, but the time you spend doing that is the time you're not spending driving your business forward. So there's some lost opportunity costs there, right? There's cost of increased regulation, right? Every time there's a big hack, what's the first thing that happens is Congress says, Oh, we need some more regulation and oversight, right? You just introduced you know, more cost there. So So when I'm talking to business leaders, I try to put it in the context of this is a risk that has to be managed, like every other risk, you're never going to get rid of this risk, right? So you have to get an understanding of what you're doing technically, but really the CIO and the size of the You need to learn it up back to our earlier discussion where you can ask pointed questions, you know, the answer isn't Bs, that when they come to the board, make sure that if the statistics they're briefing, you are not giving you a warm fuzzy that we're going the right direction, then sit down with them and figure out what do I need to be doing from a metrics perspective to understand because it's not just measuring dollars, right. But from the business leader side, the biggest thing they've got to be able to do is assume that they're going to be hacked and how are they going to respond to it? And that the business side, it's all about communication. What am I going to tell my employees first people to sue Sony were the employees. What am I going to tell my customers? What am I going to tell my partners? What do I have to tell law enforcement? What should I tell law enforcement? I'm a regulated business, what do I have to tell the regulators? You know, what is my communication plan? Right? And if the CEO gets a call at three in the morning on Sunday, and Nick has to go I'm sorry, who is this again? All right, then you have it prepared for this reach well enough right now. You haven't done that. So that's kind of the, how I try to make it an important issue that has to be worked, you know, from the business leader side. And then as you roll down from that you get into all these other basic leadership tenants, you know, how do we connect everybody to the mission? How do I provide, you know, feedback? How do we assess performance? What metrics are going to drive us? You know, what are the leading indicators, we're doing this well, how do we compare with others in the industry, you know, is all of these basic leadership tenant and then on the technical leader side, what I find that I need to do is like kind of leverage the fact that I sat no shoes for three or four years, I understand how ignored and mistreated the CIOs and the sizes of the of the world are and I thought it was bad the military but the first engagement I did and in the private sector was with a to be unnamed, large, large, large wall street bank and you know, talking to some of the business leaders and talking to this CISO staff on how they've been treated. Even I was amazed, as cynical as I was at what a gap there was in, in those two groups. And so, so I think, some cross pollenization, you know, back to the leadership thing, you know, Nick's been at our company for seven or eight years, God, we'd really like to keep him. He's up and coming, whether he's consultant or whatever it is, you know what, Nick, I'm going to, I'm going to do what they did to Gen. Williams, I'm going to send you over to work for Brian, the CIO, and you're going to work for him the next three years, and then you're going to come back. So how valuable would that be for you? Now 10 years down the road, when we're looking at making you the COO that you've got this? You're completely fluent in technology. And I'm not just talking about the cyber security. I'm talking about how do we leverage tech to move our business forward, right. Do I let every business unit bring in whatever app they want? You know, how do I Measure ROI on that, you know, etcetera, etcetera, cetera. So growing a generation, I think of leaders that is fluent in business and fluent in technology, of which one aspect of that certainly the cybersecurity, I think is part of the leadership challenge we have.

Nick Lozano  48:16
Now, I love that and Brian, I always joke that the CIO and the CISO is, you know, the other executive team just view them as the better dressed Help Desk. My phone's not getting email.

Brett Williams, Maj Gen USAF (Ret)  48:26
Yeah, soon as you walk in, right, yeah, right. Right. Right.

Nick Lozano  48:31
But that's a that's a great rundown. So I want to be respectful of your time. And you know, there's just one question that we always ask our guests, do you have a book that's had a big influence on you doesn't have to be a book. Maybe it's a piece of media HBr article or something?

Brett Williams, Maj Gen USAF (Ret)  48:45
Yeah. So I got asked this a couple of podcasts ago, and I didn't have a great answer. So I actually gave it some thought. And, and after listening to me, pontificate for the last 45 minutes, you'll you'll probably not be surprised that I don't have a single answer to that. But I give you three kind of categories of stuff that I found, amazingly impactful. So in 1993, I spent a year in a course that's another thing people don't realize the military and 33 years, I spent four full years in formal education. I mean, like, oh, professors real writing real thought. And this course was called the School of Advanced airpower studies. And it was the literally the book a day club, you met four times a seminar two hours a week, you read a book a day, and you wrote and all that. And the purpose of the course I thought at the time was to teach you, you know, it's kind of the the nexus of military strategy and politics and national strategy and those sorts of things. But what the really course was really all about was critical thinking, right is, is questioning your assumptions. It's proving that there's causation not correlation is challenging. Other people too? Is that factor opinion? Just Just tell me which one it is right? You know, those sorts of things? Because I'm interested in your opinion, but I want to know, it's an opinion, not fact. And there were two books in in that course that have that that have stuck with me. One was the essence of decision making. And what that was about was the Cuban Missile Crisis. And it went through four different models on how the US government decided to handle that. And, and it showed you really can't prove which model but you know, and I don't remember the details of that there's, there's one model that wraps around the decision was made because of the strength of the leader. There's another one that's wrapped around to actually make the organization survive politically the way it's always been bureaucratically, you know, so, so there's different models of decision making. And when you just got to realize which one is driving you to the decision and make sure that decision is okay, right. And real Realize that these are the factors affecting the decision and they may not have to do with the facts of the case. They may have more to do with the the political dynamics etc. I don't mean political as and republican democrat, I mean, traditional politics. And then the second book was called thinking in time, and it was all about how people misuse historical analogies to make decisions.

Nick Lozano  51:21
Oh, I love that book.

Brett Williams, Maj Gen USAF (Ret)  51:22
So, so think about that in the business world, right and half the time. Oh, because we were able to get into this segment of the market and deliver this product, we should have the same sales guys given the same, you know, over here, whatever the case may be, you know, it's the classic. Why are we doing it that way? Because we always did it that way. Well, that's the worst answer. It doesn't mean you shouldn't do it that way. But you really should be thinking about it. So So those two are important to me. Then the the other kind of series of things that I found are interesting is things about how humans work and how the world works, and I read a book called Sapiens. Oh, yeah, years ago. And in fact, I was at dinner this week and there was a guy at another table talking about this book sapiens, he read. I mean, the books, you know, five or six years old. I'm trying to remember the author. It's Israeli author, but Oh, Harare. Oh, yeah. Yeah. And he's written a follow on I haven't read it. But that book was fascinating to me, because it got to kind of his theory of how all of these things that we just take for granted as being facts of life, everything from money to religion to corporations, you know, that it was interesting to me because he starts from the premise of, you know, I can remember but it's about 50 people that you can keep oriented on something because we've got family ties, we live in the same town whenever when you get bigger than that, you got to have something else that gets people organized and motivated to go same direction, right. And so he went through all these these things. The other thing I read was really interesting is this book called The story of the earth. It was the author's hayson. And it was, it was mostly the geological history of the earth, but and then it touched on the biological history, the earth, but to me, there are two aspects of it that were fascinating is one, How the hell did they figure this out? It's, you know, I got a friend that says, Don't look into the abyss, but it starts getting you to think, you know, the sun's going to go out in 5 billion years, you know, and we we are a speck. I don't remember that book. It was another book, but it said if you took the entire history of the earth and put it on a calendar, right, dinosaurs showed up on like, December 12, right. Humans showed up at 12:59:30 December 31st. Right. That's how small you know. Yeah. So anyway, and then the last thing is just Really with my current efforts to, to figure out, you know, I've got all these brilliant ideas, as you all heard, but you know, how, how can I, you know, really fill my passion and figure out, you know, where can I put these to use? How can I get these out? And I started listening to a podcast by a guy named Peter Winnick, who does, he's got a company called Thought Leadership Leverage. And so he puts out a couple of podcasts a week, but he talks to people that have, you know, very well known thought leaders and doesn't talk to him about their topic, but he talks to him about all the work they had to put into all the content they had to build all the time it takes to do this, how do I target you know, how do I, you know, and all of them are, you know, are passionate about they have something they want to say. But what really motivates them is, you know, I got something I really want to talk about. Wouldn't it be cool if I could make my living doing that as opposed to nights and weekends, you know, putting out content and then go into a job which I'm in Not like as much, you know, so. So that's kind of three things that things everything that drove me to be. And I will call myself a critical thinker. I think things that make you think about put your life and our lives in perspective, I thought those couple of books were interesting. And then as I'm kind of going into this, this phase of, you know, really trying and we call it Part Three the military guys do you've got your military career, then you usually go into some kind of business and then you go into kind of a part three for some people that's they go play golf all the time, which is what I would do but I keep finding myself working out in the mornings and thinking I gotta write an article about the five things that pertain or or how to give feedback or I don't know if you guys saw the one I did on the aerodynamics of leadership I did -

Nick Lozano  55:50

  • that's what actually drove me to your profile, right? Oh my god. This is amazing

Brett Williams, Maj Gen USAF (Ret)  55:54

  • kind of thing. You know, and the one I just wrote on, we call it the debrief, you know, when you finish when you finish flying the mission, if you're going to sit down and figure out what went right, what went wrong, how to get better next time why even fly? You know, and so I talked about how much time we spent doing that. And, you know, I question from, you know, things I've seen in the private sector is, is, how well do we do? You know, I think the businesses that do best are really good at setting goals. Really good at monitoring progress towards the goals. And then occasionally, just like in Scrum and agile, right, you have a time for retrospective you stop right and you realize that's not I'm too busy working to figure out what I've been doing. Right, right. Really. Would you like to know if what you were working on was producing the results you wanted? But you know, like Yogi Berra said, if if you don't know where you're going, you might end up somewhere else. So if you don't write if you don't set goals ahead of time, then how are you going to measure progress towards them and then if you don't reach the goal, if you don't stop and take time to figure out why didn't reach Then, you know, now you're with Einstein's theory of, you know, insanity, the same thing and expect different results. But just as importantly, hey, we kicked ass on this goal. What did we do? Let's reinforce it more. Yeah, right? Or that was what we needed to do to achieve that one. Is that what we need to do to achieve the next one because we don't want to spin our wheels, right and go, Wow, we succeeded there, but now we're stuck. You know, I'm saying so, that discipline of, of what I put in that little article, plan five or plan, brief fly debrief plan, you know, that that cycle and and just, and I say ruthless and there, but I had to learn, we call it the 9010 rule is, you get into a debrief, you spend 90% of the time talking about the 10% that didn't go right. And it's because that's where we know we got to get better, right. But what I learned as you get leading these larger and larger organizations, you know, people didn't grow up with And, you know, I found, you know, my leadership style had to evolve because I found people who I had to spend more time saying, Nick, you know, I really appreciate you what you did this was really cool. This really benefit us slightly. This is one malaria that we need to you know, Brian, maybe the kind of guy that I hit him in the side of the head with two by four go, why don't you get about this? You just gotta figure out, you know, what's the best way to you know, to communicate with people to influence people and that sort of thing.

Brian Comerford  58:30
Well, clearly your size of stuff. Well, people can't see the video here, but you do look like you've been. Well Brett, thank you so much for making us part of your "Part Three." And this has been a fascinating discussion and you are definitely a critical thinker. So I really appreciate all of your contributions today. Any closing remarks, Nick about the guest that we have Here.

Nick Lozano  59:01
Oh, no, I, I'm just gonna tell you you need your own podcast. I don't know if anyone's told you that yet, but you should definitely do your own. You know, just want to thank you for your service all your time, you know, and your families. We really appreciate it. You guys keeping us safe here. And if people are looking for you on the internet, you know, you said you're a keynote speaker. You know, we'll be sure to tag everything in the show notes and information. But where can people find you?

Brett Williams, Maj Gen USAF (Ret)  59:25
I've got a couple of websites. I'm trying to figure out how I merge these personas, but the name was the cyber speaker calm. And I've got another one Brett Williams leadership. I put out most of my content really on my LinkedIn page. So either articles or comments on posts, do a lot there. And then about six weeks or so I said, I've got to get into the Instagram world. So I'm on Instagram at General at Williams and so you know, I'm figuring out how to build a A little bit of a, you know, a little bit of a following there. And so you'll see some, some posts there. And so I figure out, you know, how the pictures got to be square on that, you know? Yeah, I'm working through that. So, but yeah, basically LinkedIn is, is, you know, if you really want to see my content, that's the place to go. I'll be getting more of that onto the website. And then and then I'd love some more followers on Instagram and and now what I would really love is people on, you know, DM me on LinkedIn or Instagram, because I would always rather talk about what you want to talk about, right? So if people have stuff they want to hear about, you know, based on they've heard one of my podcasts or they've seen something, then asked it just like that guy did up there. And you know, promptly, right, five things he's told new teams. Exactly. That kind of stuff. All right. Well, I appreciate you guys. And I did I did subscribe to your podcast today. I picked out a couple that I want to listen to, for most the time in the car. So I will I'll definitely be checking you out and following you

Brian Comerford  1:00:59
It's been a real honor having you on today. Thanks again.

Brett Williams, Maj Gen USAF (Ret)  1:01:02
All right. Thanks, guys. Alright, see you later